New England’s largest city, Boston, Massachusetts, is home to historic sights and modern neighborhoods; stores and restaurants with old-time character; and gracious green spaces as well as a beautiful waterfront. Legendary figures of the American Revolution come alive at buildings and attractions along Boston’s Freedom Trail, including the Paul Revere House and Old South Meeting House, and in Lexington and Concord just outside Boston. Pay homage to great U.S. presidents at the John F. Kennedy Presidential Library and Museum and in the town of Quincy, birthplace of Presidents John Adams and John Quincy Adams. Each of Boston’s neighborhoods has its own personality and things to do, whether you’re enjoying the food of the North End’s Little Italy, admiring the beautiful 19th-century architecture of Beacon Hill or watching the street performers in Cambridge’s Harvard Square. The waterfront offers harbor views, while boat tours allow you to take in the city skyline while sightseeing. In every neighborhood, shopping and dining reveal Boston’s true eclectic self, from casual to high-end, but always interesting. Finally, Boston is a city of green spaces where you can relax and enjoy the outdoors. The Emerald Necklace, designed by Frederick Law Olmsted, is a 445-hectare (1,100-acre) chain of nine linked parks, including the lovely Boston Common and Public Garden.

Your visit to Portland and the English countryside of County Dorset will be rich in scenic beauty and centuries-old history. Visit the ancient village of Cerne Abbas and admire its beautiful 14th-century church and 16th-century houses; explore Sherbourne Castle, commissioned by Sir Walter Raleigh in 1594; and marvel at prehistoric Stonehenge, a UNESCO World Heritage Site. Sample shore excursions: Historic Corfe Castle; Stonehenge & Salisbury; Stunning Sherborne Castle.

Saint John, on the southern coast of New Brunswick, is Canada’s oldest incorporated city as well as the only city on the Bay of Fundy. Give your stroll through uptown Saint John a little focus by taking the self-guided Loyalist Trail walking tour, which visits historic attractions like the 1784 Burial Grounds, the 1876 Old City Market, a general store and the Jewish Historical Museum. The New Brunswick Museum, also along the Loyalist Trail, tells the story of the town and exhibits cover some of its natural history, too, with an 80,000-year-old mastodon skeleton. The Martello Tower has been part of Saint John’s identity since it was erected for the War of 1812; it was even used to house prisoners during World War I. The most exciting part of your trip to Saint John may be your chance to view the point at which the Bay of Fundy and the Saint John River collide: the Reversing Falls Rapids. If simply observing the churning waves and whirlpool is not enough, ride a zip line over the waters for added thrills.

Located on a rocky inlet on the Atlantic Ocean, Halifax—Nova Scotia’s provincial capital—is defined by its maritime geography. It’s a spirited mix of world-class history and nautical-themed museums alongside bunkers and fortresses that guarded the harbor, plus striking public art and sights, funky shops and excellent pubs serving up folk music (and good pints). Explore the Halifax waterfront where steamships once anchored to drop off arriving immigrants at Pier 21. Savor the low-key but classy culinary scene for fresh seafood and Nova Scotia specialties—the city has both street vendors and casual joints catering to university students and upscale eateries with elegant settings. Along Nova Scotia’s southern shores, the city is surrounded by lush greenery and charming villages that are worth the trip from downtown proper. Snap photos of attractions in the charming fishing village, Peggy’s Cove, with its picturesque lighthouse on a rocky outcropping. Or wander the streets of Lunenburg, whose colorful Old Town is designated a UNESCO World Heritage Site. You can also soak in the charms and sights of Mahone Bay, home to artists’ studios and a trio of steepled churches.

Corner Brook, a small but bustling city, is on Newfoundland’s west coast. Captain Cook initially mapped this area, known as the Bay of Islands, in 1767, and like many other Newfoundland settlements, Corner Brook started out as a fishing village. Later, one of the largest pulp and paper mills in the world was built here. In the city’s downtown core, West Street and Broadway are the center of action, thanks to numerous pubs, shops and restaurants. The local university has renowned fine-arts and drama programs, so you’re never too far from entertainment. Corner Brook also has an impressive amount of green space—you’re always within walking distance of a park or trail. Nearby Humber Valley and the Marble Mountain offer some of the best skiing in Atlantic Canada, a big enticement for outdoor-adventure junkies. Even if you’d prefer to just take in the scenery, the rolling green mountains and the views overlooking the bay are worth the trip.

Charlottetown is the capital of Canada’s smallest province, Prince Edward Island, as well as its largest city, though it has fewer than 35,000 residents. Despite its modest size, the city has an impressive number of Victorian houses and buildings and great parks waiting to be explored. For Canadians, it is perhaps most famous as the Birthplace of Confederation. It was here, mostly at Province House, that an 1864 conference led to the creation of the Dominion of Canada. Prince Edward Island is linked to New Brunswick on the mainland of Canada by the 13-kilometer (eight-mile) Confederation Bridge that soars over the Northumberland Strait. A remarkable feat of engineering, the bridge opened in 1997 and is the longest in the world over icy waters. Sites within downtown Charlottetown include the lovely Victoria Row, which becomes a pedestrian mall each summer, and other historic buildings, some of which are now museums. Nearby Prince Edward Island National Park is home to white-sand beaches and hiking and biking trails—plus fans can see the house and farm that inspired the beloved book Anne of Green Gables. During your visit, you can also learn about the daily lives, past and present, of residents on lighthouse and boat tours.

Gorgeous, green and Gallic, this charming village is your gateway to some of the most stunning scenery in North America: majestic fjords, dramatic rocky capes and picturesque hamlets are all here. So are artisans of every ilk, from glassblowers to angora goat farmers. Sample shore excursions: Saguenay Village Highlights; Saguenay National Park by Zodiac (or Seaplane); The Craftsman Road.

Few places in North America are as steeped in history as Québec City, Canada. Older than Jamestown and founded before the Pilgrims landed at Plymouth Rock, it is the only city north of Mexico whose original fortifications remain intact. The Québec City historic district, a UNESCO World Heritage Site, is still home to religious orders and hospitals that date back to the 17th century. Its Place-Royale would look familiar to the explorer Samuel de Champlain, even with its modern attractions of gift shops and cafés. On the Plains of Abraham, you can walk the battlefield where, in 1759, the French forces under General Montcalm were decisively trounced by the British, led by General Wolfe. The British took control of all of New France within a year of that 1759 battle, but even so French culture still lives on here in Québec City. More than 95 percent of Québec City’s population speaks French as its first language, though it’s easy to sightsee and navigate the city in English. As you tour the museums and historic sights of Québec City that celebrate Québecois history and dine at restaurants that serve its distinctive cuisine, you’ll discover a remarkable culture that has survived and thrived into the 21st century.

Montréal, Canada is a city of contrasts, one that defies a simple description or a catchy tagline. It sits on the New World’s St. Lawrence River, yet it has an undeniable Old-World French flair. It is a historic city, founded in 1642, and the streets of Old Montréal are lined with sights that range from a 17th-century seminary to grand commercial buildings erected in the 19th century. But Montréal is also home to contemporary architectural masterpieces—most notably those erected for Expo 67, including Buckminster Fuller’s Biosphere. Montréal is at once the cultural capital of the Québecois and a decidedly global and cosmopolitan city, attracting migrants from around the world. The walls of its galleries and museums showcase leading artists from the province and the rest of Canada, while the city hosts festivals that feature the best international films, musicians and performers. Many of its restaurants serve traditional specialties—poutine, bagels and smoked meats; others are helmed by some of the continent’s most innovative chefs. Montréal is a vibrant urban center, with buzzing streets and attractions, yet crowned by peaceful, leafy Mount Royal Park, designed by Frederick Law Olmsted (also responsible for New York’s Central Park). Whichever of the city’s many aspects appeals to you most, you are sure to be charmed by this unique city and find many things to do in Montréal.